Assuming that what you're stating is all checks out, you should easily qualify with a lender who doesn't have conventional overlays. 

Check. 

Quote from @Zachary Deal: may be worth just handling all bookings through Airbnb or VRBO to add some level of protectionIf booking outside these platforms, we use KeyCheck to run background and credit checks on tenants, but we may switch to Rent Redi as they collect the tenant's photo ID for you as well. 

As for mentoring, maybe check out local investment clubs or online communities like Reddit's investing or personal finance subs.

During Covid  other loan types got modification deals, not so much with VA loans.Department of Veterans Affairs is going to review every file with one late payment and check the deed, check the fire insurance.

I'm not a pro, but I'd start by checking out what similar places in your area are doing.

To find vacant land, check real estate websites, local listings, or work with a real estate agent.

You could check us out, if you need someone even smaller I can try to find someone to recommend. 

Maybe checking out local networking events or online forums could help you connect with potential lenders.

Depends on your state laws so check that out.